4-环己基苯磺酰氯 | 56354-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-环己基苯磺酰氯
• 英文名称: 4-cyclohexyl-benzenesulfonyl chloride
• 英文别名: 4-cyclohexylbenzene-1-sulfonyl chloride；4-Cyclohexylbenzenesulfonyl chloride
• CAS: 56354-57-5
• 化学式: C₁₂H₁₅ClO₂S
• mdl: MFCD00625713
• 分子量: 258.769
• InChiKey: CREMYEDHKUWVTB-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54℃
• 沸点：
  358.5±21.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险等级：
  8
• 海关编码：
  2904909090
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P280,P301+P330+P331,P302+P352,P304+P340,P305+P351+P338,P310
• 危险品运输编号：
  3261
• 危险性描述：
  H314
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Cyclohexylbenzenesulfonyl chloride
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Cyclohexylbenzenesulfonyl chloride
CAS number: 56354-57-5

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H15ClO2S
Molecular weight: 258.8

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen chloride, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
UN Number: UN3261 Class: 8 Packing group: III
Proper shipping name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. (4-Cyclohexylbenzenesulfonyl chloride)

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-环己基苯磺酰氯 在 potassium phosphate 、 potassium hydrogen difluoride 、 palladium diacetate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 氢化三联苯
  参考文献：
  名称：

  “唤醒”芳基磺酰氟：铃木-宫浦偶联反应的新伙伴

  摘要：

  使用 Pd(OAc) 2催化的 Suzuki-Miyaura 偶联反应中的新伙伴描述了 -SO 2 F 基团的活化示例，该基团传统上被认为即使在存在过渡金属的情况下也是稳定的基团，并且Ruphos 作为配体。产品在最佳条件下表现出良好至出色的收率和广泛的官能团相容性。非对称三联苯的顺序合成和克级工艺突出了该方法的合成效用。DFT 计算表明 Pd 0更喜欢插入 C-S 键而不是 S-F 键之间。

  DOI：

  10.1039/d1nj05469d
• 作为产物：
  描述：

  环己基苯 在 氯磺酸 作用下， 以 氯仿 为溶剂， 反应 0.75h， 生成 4-环己基苯磺酰氯
  参考文献：
  名称：

  通过基于计算机/片段的铅鉴定和从头修饰铅，对某些选择性的基质金属蛋白酶-2抑制剂进行了稳健的设计，使其优于基质金属蛋白酶9：合成和生物学检测。

  摘要：

  广泛的选择性严重限制了用于临床目的的基质金属蛋白酶2（MMP-2）抑制剂的开发。为了开发有效的和选择性的MMP-2抑制剂，最初采用了多种分子建模技术来进行可靠的设计。使用预测性和经过验证的回归模型（2D和3D QSAR和基于配体的药效团作图研究）来估计效价，而分类模型（贝叶斯和递归分配分析）用于确定MMP-2抑制剂对MMP-9的选择性。贝叶斯模型指纹用于设计选择性先导分子，并使用基于结构的从头技术对其进行修饰。制备了一系列设计的分子，并分别针对MMP-2和MMP-9的抑制作用进行了筛选，因为这些是紧随其他MMP之后设计的，以观察到更广泛的选择性。最佳活性MMP-2抑制剂的IC50值为24nM，而最佳选择性抑制剂（IC50 = 51nM）对所有测试的MMP表现出对MMP-2的选择性是至少4倍。活性衍生物对人肺癌细胞系A549无细胞毒性。在非细胞毒性浓度下，这些抑制剂最多可将细胞内MMP-2表

  DOI：

  10.1016/j.bmc.2016.07.023
• 作为试剂：
  描述：

  4-Cyclohexylbenzenesulfonic Acid Sodium Salt 、 五氯化磷 、 在 二氯甲烷 、 4-环己基苯磺酰氯 、 crude product 作用下， 反应 8.0h， 生成 4-环己基苯磺酰氯
  参考文献：
  名称：

  Substituted saccharin compounds and curable compositions containing same

  摘要：

  一种可固化组合物，包括至少具有一个可固化丙烯酸官能团的单体，加速剂和可选的自由基引发剂，其中加速剂是以下式子的化合物：##STR1##其中R'为H或烷基；当R'为H时，R为取代或未取代的环己基，烯基氨基或C.sub.3-C.sub.10支链烷基；当R'为烷基时，R为芳基烷基。这样的组合物可用作固定（例如，螺纹锁定）组合物，并克服了在有机非极性介质中溶解度差和使用糖精本身作为加速剂时与温度有关的问题。还公开了相应的聚合含有丙烯酸官能化合物的组合物的方法，以及从相应的取代苯磺酰胺制备取代糖精化合物的方法。具体公开了烯基酰胺取代的糖精化合物和烷基、芳基烷基二取代的糖精化合物。

  公开号：

  US04764239A1

文献信息

• The Design and Synthesis of N-Xanthone Benzenesulfonamides as Novel Phosphoglycerate Mutase 1 (PGAM1) Inhibitors
  作者：Penghui Wang、Lulu Jiang、Yang Cao、Deyong Ye、Lu Zhou

  DOI：10.3390/molecules23061396

  日期：——

  Upregulation of phosphoglycerate mutase 1 (PGAM1) has been identified as one common phenomenon in a variety of cancers. Inhibition of PGAM1 provides a new promising therapeutic strategy for cancer treatment. Herein, based on our previous work, a series of new N-xanthone benzenesulfonamides were discovered as novel PGAM1 inhibitors. The representative molecule 15h, with an IC50 of 2.1 μM, showed an enhanced PGAM1 inhibitory activity and higher enzyme inhibitory specificity compared to PGMI-004A, as well as a slightly improved antiproliferative activity.

  磷酸甘油酸变位酶1（PGAM1）的上调已被发现是多种癌症中的一个常见现象。抑制PGAM1为癌症治疗提供了一种新的有希望的策略。基于我们之前的工作，我们发现了一系列新的N-呫吨酮苯磺酰胺化合物作为新型PGAM1抑制剂。代表性分子15h，其IC50值为2.1 μM，与PGMI-004A相比，表现出增强的PGAM1抑制活性和更高的酶抑制特异性，同时其抗增殖活性略有提高。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：CTXT PTY LTD

  公开号：WO2019243491A1

  公开（公告）日：2019-12-26

  A compound of formula (I), or a pharmaceutical salt thereof.

  式(I)的化合物，或其药用盐。
• [EN] SMALL MOLECULE INHIBITORS OF MCL-1 AND USES THEREOF<br/>[FR] PETITES MOLÉCULES INHIBITRICES DE MCL-1 ET LEURS UTILISATIONS
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2016172218A1

  公开（公告）日：2016-10-27

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having benzoic acid structure which function as inhibitors of Mcl-1 protein, and their use as therapeutics for the treatment of cancer and other diseases.

  这项发明属于药物化学领域。具体来说，该发明涉及一类具有苯甲酸结构的新型小分子，其作为Mcl-1蛋白的抑制剂，并且它们作为治疗癌症和其他疾病的药物的用途。
• Xanthone derivatives as phosphoglycerate mutase 1 inhibitors: Design, synthesis, and biological evaluation
  作者：Penghui Wang、Lulu Jiang、Yang Cao、Xiaodan Zhang、Bangjing Chen、Shiyu Zhang、Ke Huang、Deyong Ye、Lu Zhou

  DOI：10.1016/j.bmc.2018.02.044

  日期：2018.5

  Phosphoglycerate mutase 1 (PGAM1) is a glycolytic enzyme that dynamically converts 3-phosphoglycerate (3PG) to 2-phosphoglycerate (2PG), which was upregulated to coordinate glycolysis, pentose phosphate pathway (PPP) and serine biosynthesis to promote cancer cell proliferation and tumor growth in a variety of cancers. However, only a few inhibitors of PGAM1 have been reported with poor molecular or

  磷酸甘油酸突变酶1（PGAM1）是一种糖酵解酶，可将3-磷酸甘油酸（3PG）动态转化为2-磷酸甘油酸（2PG），后者被上调以协调糖酵解，磷酸戊糖途径（PPP）和丝氨酸生物合成，从而促进癌细胞增殖和肿瘤。各种癌症的生长。然而，据报道仅有少数PGAM1抑制剂具有较差的分子或细胞效力。本文通过基于铅化合物PGMI-004A的脚手架跳跃和磺酰胺逆转策略，发现了一系列黄嘌呤衍生物作为新型PGAM1抑制剂。大多数x吨酮衍生物比PGMI-004A对PGAM1的效力更高，并且在不同的癌细胞系中表现出中等的抗增殖活性。
• Three-Component, Interrupted Radical Heck/Allylic Substitution Cascade Involving Unactivated Alkyl Bromides
  作者：Huan-Ming Huang、Peter Bellotti、Philipp M. Pflüger、J. Luca Schwarz、Bastian Heidrich、Frank Glorius

  DOI：10.1021/jacs.0c03239

  日期：2020.6.3

  (tertiary) alkyl halides remains an unmet challenge owing to unavoid-able β-hydride elimination. Herein, we show that a modular, practical and general palladium catalyzed, radical three-component coupling can indeed overcome the aforementioned limitations through an interrupted Heck/allylic substi-tution sequence mediated by visible light. Selective 1,4-difunctionalization of unactivated 1,3-dienes, such

  开发有效和选择性的策略来处理包含（多）立体中心的复杂架构，一直是学术界和工业界的一个长期综合挑战。催化级联反应代表了一种从简单原料中快速利用分子复杂性的有力手段。不幸的是，由于不可避免的 β-氢化物消除，进行涉及未活化（叔）烷基卤化物的级联 Heck 型反应仍然是一个未解决的挑战。在此，我们展示了模块化、实用且通用的钯催化的自由基三组分偶联确实可以通过可见光介导的中断的 Heck/烯丙基取代序列克服上述限制。未活化的 1,3-二烯（如丁二烯）的选择性 1,4-双官能化，通过使用不同的市售氮基、氧基、硫基或碳基亲核试剂和未活化的烷基溴（>130 个实例，大多数 >95:5 E/Z，>20:1 rr）实现了这一目标。连续的 C(sp3)-C(sp3) 和 CX (N、O、S) 键已被有效构建，具有广泛的范围和高官能团耐受性。该策略的灵活性和多功能性已在复杂醚、砜和叔胺产品的克级反应和流线型合成